What would be the final product,F,of the following sequence of reactions?
A)1-Bromo-2-methyl propane
B)3-Bromo-3-methylbutanoic acid
C)Butanoic acid
D)3-Methylbutanoic acid
E)Methyl 2-methylproanoate

Question

What would be the final product,F,of the following sequence of reactions? 
A)1-Bromo-2-methyl propane 
B)3-Bromo-3-methylbutanoic acid 
C)Butanoic acid 
D)3-Methylbutanoic acid 
E)Methyl 2-methylproanoate

Quizplus · Accepted Answer

The given sequence of reactions involves oxidation, bromination, and hydrolysis. The starting material is a methyl alkane, which upon oxidation with KMnO4 gives a carboxylic acid with one fewer carbon atom. Therefore, option C (butanoic acid) cannot be the final product. Next, the carboxylic acid is brominated using PBr3, leading to the formation of an alkyl bromide with the same number of carbon atoms. This eliminates options A and E. Finally, the alkyl bromide is hydrolyzed using aqueous NaOH, leading to the formation of a carboxylic acid. The product is an isomeric mixture of 2-methylbutanoic acid and 3-methylbutanoic acid. However, since the starting material is a branched alkane, the major product is 3-methylbutanoic acid. Hence, the final product is option D (3-methylbutanoic acid).

What Would Be the Final Product,F,of the Following Sequence of Reactions